Hydrochloric Acid → 7-chloro-3-(2,6-dichlorophenyl)-4-imino-1-methyl-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one

HRID 2088727Notes

Reaction equation

HRID 2088727 reaction equation
[C:1](=[O:4])([O-])[O-].[K+].[K+].CI.[Cl:9][C:10]1[N:15]=[C:14]2[NH:16][C:17](=O)[N:18]([C:21]3[C:26]([Cl:27])=[CH:25][CH:24]=[CH:23][C:22]=3[Cl:28])[C:19](=[NH:20])[C:13]2=[CH:12][N:11]=1.Cl>C(OCC)(=O)C.CN(C)C=O>[Cl:9][C:10]1[N:15]=[C:14]2[N:16]([CH3:17])[C:1](=[O:4])[N:18]([C:21]3[C:22]([Cl:28])=[CH:23][CH:24]=[CH:25][C:26]=3[Cl:27])[C:19](=[NH:20])[C:13]2=[CH:12][N:11]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 178507161HCID 178507161, compound

Product 1

HCID 582897897-chloro-3-(2,6-dichlorophenyl)-4-imino-1-methyl-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-oneYield 67.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

484 mg of potassium carbonate and 456 mg of methyl iodide were added to an N,N-dimethylformamide (5 mL) solution of 1.00 g of 7-chloro-3-(2,6-dichlorophenyl)-4-imino-3,4-dihydropyrimido[4,5-d]pyrimidin-2(1H)-one obtained in Production Example 1, and stirred at room temperature for 1 hour. The reaction solution was added to ethyl acetate and aqueous 0.5 N hydrochloric acid solution with stirring, and the organic layer was separated. This was washed with saturated saline water, dried with anhydrous sodium sulfate, and the solvent was evaporated away. The crude product was solidified from chloroform/methanol/hexane to obtain 700 mg of the entitled compound as a yellow solid.

Workup

  1. customobtained in Production Example 1
  2. stirringwith stirring
  3. customthe organic layer was separated
  4. washThis was washed with saturated saline water
  5. dry with materialdried with anhydrous sodium sulfate
  6. customthe solvent was evaporated away

Sources & evidence

ORD record
ord-e848033b1b7743419a3b8293468155d1
Source dataset
uspto-grants-2013_05
Patent number
US08436004B2

Reaction notes

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